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Greg Fitzsimmons started doing stand up in Boston but moved to New York shortly thereafter. He made his stand-up television debut in 1996 on Late Show with David Letterman and since that time has steadily honed his Irish sensibilities onstage, appearing on multiple other shows and networks in the process. He just released his new book, Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox, a personal yet funny memoir shaped around the letters and documents his mother kept from throughout his life. I spoke with Greg over the phone about the book, his stand-up and more.

When I heard about the book, I figured it would be about stand-up and your early years, but it’s actually more about your relationship with your parents.

I think there a lot of comedians with books out there and people go different ways with it. With me being Irish, I felt compelled to go deep into the heavy stuff as well as how I became a comedian and try to put funny stuff in it.

There are a lot of moments that are like origin tales of how you became a comedian, but it’s more in very early stages. You have stuff about your first open mics, but the book has more material about the things influencing you to get into comedy.

I was trying to get to what shaped my personality. Where the pain came from, where the excitement came from. The dynamic of comedians butting up against the line of what’s acceptable and dangerous. I didn’t really get into the fact that I have ADHD in the book. I almost feel like that’s the next book. I think that it’s as much about circumstance as it is about DNA almost.

You feel like it was more DNA that influenced you to become a comedian?

I think it’s both. In that last chapter, when I get into what my kids are like, the punchline is that there’s only so much you can really change.

You mention in the book that your father would maybe have been a comedian had he been born in a different time. He was in radio and was an entertainer, but he probably would have been closer to what you do.

I think so. In watching him, the part of him I saw more was when he would MC things. Seeing his personality up close. That was the thing I saw where the dynamic was really working. I always felt like he was a great radio guy, but that was a bottled version of his personality. When I started watching stand up as a kid, it was like it took more balls. But it was also available to me in a way that wasn’t in his generation. I think Irish storytelling, whether in the radio or in a comedy club is very similar. When I do my radio show, I don’t approach it any different than I approach stand-up. I just take longer pauses, because I’m alone and it’s a slower pace.

You’ve mentioned there are two kinds of comedians, the kind who try to cater to audiences and the kind that come with their own point of view.

I have comedians who come up to me and are starting out, or not even starting out, like they haven’t even done it yet, and they ask me how to get started, how you can make money, how to get an agent. Guys that have been doing it for a year or two asking me how to make it on Last Comic Standing so they can get exposure. What are you trying to expose? You got nothing to expose yet. It takes fifteen years to get really good at stand-up.

It was never about the money to me. It was about having to do it. It was like nothing else would hold my attention and my passion the way I knew stand-up would. It was never like, I am going to do this forever for a career. It was more like, at this moment, in my life, I have to do this thing. And then you look up, twenty years later, and you’re like, “Oh my God. I have a mortgage and a wife and kids and cars and we go on family vacations. And it’s all paid for by me telling dicks jokes to people eating chicken wings.”

How important do you think going out on the road, rather than just staying local, shapes a comic?

I think the fear level when you’re on the road recreates the origins of comedy. Mostly we’re funny as a reaction to an uncomfortable situation. Whether Dad’s dead drunk and everyone’s at the dinner table, or you’re screwing up in school so you get a laugh to get some acceptance instead of looking like a failure all the time, asking a girl out and she says no and then you’re laughing about it with your friends, a lot of it comes from an uncomfortable place.

When you say “staying local,” I almost think of the words “alternative comedy.” It’s really an alternative to commercial comedy. I think that’s a pretty accepted definition of what the genre is. To me there’s not a lot of fear with that. I do these alternative shows and it’s filled with like-minded, for lack of a better word, hipsters, who are white and college educated, urban-cool. It’s a clique. As opposed to going on the road and facing people who have worked jobs they don’t like all week, and now it’s the weekend and they need a laugh. And they are spending money. Your job is to go up there in front of a cross-section of real America and to get a laugh first. You’re not there to talk politics. You’re not there to say ironic things about pop culture, because people don’t give a shit about that outside of New York and LA. And granted, you might make a point, which I think I do because I talk about things that are truthful to me and things I am feeling, but I feel like staying in a city as a comedian doesn’t demand you to go to a place where you can grow as a comic.

When people first start doing road work, it can almost be like starting over. Like starting at mics and bombing again.

There’s a lot of other factors. You can talk about going onstage, you also have to get the gig, which means hustling, sending a tape, following up with calls, emails, getting someone to recommend you. Then you get the gig; you’re on a tight budget. When you’re a feature act, you’re only making five, six, seven hundred bucks a week. And that includes getting yourself to another city, sometimes housing yourself, finding a friend to stay with. Then you have to find transportation. Then you have to get to the club and you have to do the right thing with the manager and the headliner. There’s a lot of do’s and don’ts to learn. It’s real life. It’s not like being in LA: you drive your car to a coffee house, and you schmooze with your buddies in the back, and you do ten minutes, and you crack up some people like you. This is the real world, on the road. You have to learn to do morning radio, get up at five o’clock in the morning and sit in the studio with a bunch of shock jocks while they are trying to be funnier than you are. And are you going to drink too much or are you going to write material. It’s a bunch of dynamics in place that go way beyond the material and the crowd.

You started around the comedy boom. You write about doing eight sets a night, which isn’t really how it works now. Do you think that environment, doing that many sets, might have created a certain kind of comic we don’t see anymore?

I have to always be careful not to compare comedians starting today with how I started, because I was extremely fortunate to start right in the sweet spot when legitimate clubs came up in a lot of cities and the pay-scale was good because there was almost more demand than there was product.

Doing that number of spots is pretty specific to New York City. When I was in Boston, I would maybe do three sets a night, which is all I could do because I would drive from place to place. And in New York, I just did Letterman last week, and I ran out on the weekend before, and I did five, six, seven sets a night at the club, just doing my five-minute set. It’s still possible, and it still comes down to, again, a demand.

If you are a comic and you’re just starting out, but you can consistently go onstage and keep an audience’s attention and close strong, you’re going to get work. You’re going to get sets. You’re going to start out doing it for free in places with ten people, but you’re going to be meeting people. Like when I came up, I was struggling, and I was coming up at the same time as Jim Gaffigan, Sarah Silverman, Greg Giraldo and Jeffrey Ross. And we were just telling each other about coffee houses up by Columbia University where you can do a set. We would tell each other about places that would let us get on. That was it.

And you can form a bond with these people that, to this day, I can call these people to come in and do my podcast or my radio show and we still compare notes. Again, it’s not always what goes onstage, but when you’re doing it and you’re coming from the right place, the love of stand up, you find like-minded people and that’s a big part of what supports your career.

Is it different now that people are starting to have families and having kids among the people you started with?

We don’t see each other as often, but it’s very meaningful when we do. Giraldo dying is something that impacted us almost as much as a family member. Because there’s that piece of your life and that shared history. It’s hard to understand that it’s just gone. I will never have a history with a group of people like I did with the ones I came up with.

It’s very hard when you have a family, you don’t have downtime to hang out. When I do a set now, like at The Improv, I’ll get there five minutes before my set, and I will literally get offstage and put my head down and walk through the bear area, because I just don’t have time to hang out and talk to people. I need to get home, because I’m on the road so much that if I’m going to do a set in town, it’s just do the set in town.

That’s why I love benefits, because you’ll go and you’re helping out a good cause, but you’re with your peers. When you’re on the road, it’s with an opener you don’t know and a feature act you may or may not know. But when I do a benefit, I’m there with Dave Attell and Louis CK and people that I cherish every moment that we’re hanging out and talking together.

You’ve mentioned that being edgy to you isn’t just being racist, it actually comes from being honest and saying things you’d be embarrassed to say.

I think there’s shocking and I think there’s edgy. Edgy to me seems against convention. It’s not caring about the rules, including like when I started talking about my kids, when Louis CK started doing jokes about his wife and kids. People didn’t do that, because that was considered old school. It wasn’t cool. It showed your age. It showed you not being edgy. The truth is, the only thing that matters is you’re talking about what’s going on in your life. You’re sharing your embarrassing moments, and you’re exploring your discoveries in life as you’re having them. Whether or not you think people will relate to them doesn’t matter. All that matters is you’re going as deep as you can into your own reality. And at this point, having the skills to make a connection to an audience. So edginess to me means, every time I go onstage, thinking, “What can I talk about that I would be embarrassed telling my best friend?” That’s my criteria for where a good joke is going to start.

Not that every joke is going to start with that. Some of the thoughts are like, man, no one has ever talked about this. Like I was doing a bit this weekend about the NAACP calling the Tea Party racist. Which, it is, but I think the Tea Party missed an opportunity to say, ‘Wow, we feel really bad about that. Let us make it up to you by writing a check to your organization. How do you spell ‘colored’ again?’

And saying the word “colored” onstage in front of a mixed audience, that’s edgy. It’s not shock value, because there’s a specific and truthful intent, which is, I hate the word police. I don’t think semantics should be on the table in terms of race relations. I think the people that put it there are the ones creating the real problems. And deciding what groups can say what about who and when a term changes from negro to colored to Afro-America to African American to black. It’s like they should have a website where every thirty seconds, you can go look and see, “Can a Latino say the N-word? Well, yes, but only if they’re urban but not an immigrant. And an immigrant needs to be called Latino, not Mexican. But not Hispanic, because they’re not all from Spain.” And it’s bullshit.

A comedian’s job is to say their first thought. When I see a black guy with an Asian woman, what’s my first thought? “Well, maybe they met during war time.” And that’s stupid and simple, but I thought it. If I thought it, I can say it onstage, and I can explore my reaction to what I said. But I realize that’s stupid, but in saying it I’m probably expressing something that other people also thought but never had the guts to say.

There’s something edgier to you admitting to having a racist thought over making an ironic racist joke.

It’s very safe to make an ironic racist joke. It’s very wink-wink, I’m playing a character, I’m exploiting this, as opposed to, here’s a very real thing that I see out there. When I see an Asian guy, I feel like, “This poor bastard.” Because Asian woman are dating white guys and black guys. It’s very, very rare to see an Asian guy out with a black woman or a white woman. Now that’s something we see and how much we process it really depends on how often you see it. But there is a level to which everyone has seen that. And I know that because when I say it, people laugh. And when I say it, the Asian people in the audience laugh the hardest. I’m not in the business to change people’s minds and to make the world a better place. I’m just in the business to have original thoughts and to find a creative way to express something and to hear laughter. That’s it.

Do you think there’s a bit of a tension breaking there causing that laugh?

I think when a guy in a wheelchair is in the front there because that’s the only place they can place him, at some level, that guy has to be aware people are looking at him, not just as a guy, but as a guy in a wheelchair. So when I walk out and go, “Wow, you have the beast seat in the house, because if you don’t like where you are, you can always move,” that’s something acknowledging the reality of what’s happening in a room. That’s what good comedy is. It’s like good acting. It’s being in the moment. It’s being truthful.

At the end of the hour, I can take a crowd that may have a whole different bunch of dynamics going on; someone’s on a first date, there’s a bachelorette party, there’s a mixed-race couple, and everyone has a different agenda for what’s funny—but if I can go and break apart things and be honest about things, I can feel them gelling and becoming one group for the hour. It might take me five minutes, it make take me forty minutes to try to break those walls down, until it’s almost like a herd of cattle. And you have them all moving in the same direction as a group. And it carries you. There’s nothing I can say that won’t get a laugh or keep their interest, because I’ve broken the walls down, and I’ve done it in a way that broke the tension. Now they trust me and they trust that I’m going to go to some uncomfortable places, like death, AIDS, 9/11 and topics not discussed, where tension is buried in. And by confidently bringing them through and getting a laugh with it, the trust keeps building and building. So by the end, it’s an amazing feeling. Almost like diving into a crowd and having them pass your body around. That’s what it feels like by the end of it.

Greg does the podcast from New York this week with comedian Brian Regan. Brian talks a little about his family life, and his very regimented work schedule. Greg and Brian are much more comfortable with self effacing stories compared with stories where that person is the hero, which leads to how “Overheards” was created. They talk about how quickly they’ll judge a tv show that effort, time and money has been poured into, but stick with any porn almost instantly. They talk about dealing with comedy crowds, and trying to do one better than the crowd. Greg wraps up the podcast by announcing that his book, Dear Mrs. Fitzsimmons, is out.

All this week, standup comic Greg Fitzsimmons will be filing dispatches from the promotional tour for his very funny, kinda memoir-y new book, “Dear Mrs. Fitzsimmons: Tales of Redemption From an Irish Mailbox.”

For me, today marks the beginning of a celebration after two years of hard work. I will tape an appearance on “Late Show with David Letterman” tonight (airing Friday). Tomorrow, I head into “The Howard Stern Show.” Over the next few weeks I will do dozens of radio interviews and talk shows including “Jimmy Kimmel Live,” “Chelsea Lately” and NPR. My mission: to promote a book I wrote titled, “Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox.”

The book tracks my lifelong problem with authority, starting with my father and continuing with teachers, the police and eventually standup comedy audiences. I hope to now focus on Irish Americans the light that has long been shined upon the insular world of Italian Americans through “The Sopranos” and “Goodfellas.” An urgent rebelliousness undermines our otherwise charming exterior, one that causes us to, almost without exception, do exactly the opposite of whatever we are told to do.

The book tracks my teachers’ reactions to this spirit through the letters they sent home to my parents. The innocent teachers hoped that my parents would reprimand me and help keep order in their classroom. How could they know that the letters were met instead with howls of laughter? There was an (implied) encouragement that I return to school and somehow generate more humorous notes for my family to enjoy.

Nietzsche said that whatever doesn’t kill you makes you stronger. After you turn forty, however, I think that whatever doesn’t kill you just makes you pissed off at whatever almost killed you. I could’ve avoided months of poring over my history of painful failures had it not been for my agent and an unintentionally hilarious complaint he received about me more than a decade ago. This one was postmarked from a small high school in the Midwest. I had performed my comedy act at their senior prom and had left a real impression on them. In the words of the principal, “what we try so hard to instill in our young people can be dashed in one hour by some ‘comedian’ who can leave town after doing his damage.”

I began reading the letter to comedy audiences and, like my parents, the crowds encouraged me to generate more comedic missives. (Click here to read the letter.) But thanks to my mother’s scrapbooking skills, it turns out I didn’t need to. She handed over a box of letters she’d saved spanning my entire life. The trove began in preschool (literally) and continued through college, where I was charged with “assault with a deadly weapon” my freshman year.

This treasure trove of material was the basis for a one-man show I performed a decade ago in Manhattan only twice before shelving the idea. It was brought back to life two years ago when I was approached by a literary agent wondering if I had any ideas for a book. What ensued were missed deadlines, self-hatred and eventually a book that I will be furiously peddling until I am told to stop.

I will sleep late today after rehearsing my Letterman set in five different clubs on Sunday night. The first time I appeared on his show was without a doubt the high point in my professional life and I take it just as seriously now even after doing the show a handful of times since. Whether it helps sell a lot of books or not, it feels pretty good to know that in a few hours my hero is going to be holding in his hand a book that I wrote. That part might actually make me stronger.

—Greg Fitzsimmons

Read More http://www.gq.com/blogs/the-q/2010/11/comedian-greg-fitzsimmons-guest-blogs-his-way-through-a-book-tour-volume-1.html#ixzz15eiU3Tfh

Your memoir, Dear Mrs. Fitzsimmons: Tales of Redemption From an Irish Mailbox, is out November 9. Given the years of relative hell you put her through, what does your mother now think of your career as a successful comic?

For an Irish mother there’s two realities. One is, “My son is successful.” That’s the headline. And then there’s the reality where …

Master of the whip, Verizon FMX rider Todd Potter joins comedian Greg Fitzsimmons and the lovely Michelle Nunes from Foxsports.com and FUEL TV show “Cubed,”. They rap about Metal Mulisha tattoos on sexy superfans and take a look at the most insane motorcycle prank we’ve ever seen. All that and drummer of Slipknot, Joey Jordison, rips up the Stride Sound Stage with his insane supergroup Murderdolls.
Airing Tuesday, November 2 at 9:30 pm Eastern Time (6:30 pm Pacific Time) Greg will appear on “The Daily Habit.”

Master of the whip, Verizon FMX rider Todd Potter joins comedian Greg Fitzsimmons and the lovely Michelle Nunes from Foxsports.com and FUEL TV show “Cubed,”. They rap about Metal Mulisha tattoos on sexy superfans and take a look at the most insane motorcycle prank we’ve ever seen. All that and drummer of Slipknot, Joey Jordison, rips up the Stride Sound Stage with his insane supergroup Murderdolls.

Greg is rolling solo for this weeks podcast where he entices Americans not to vote, he name drops all the celebrities his kids got candy from, and he talks about the hecklers he encountered in West Palm Beach. Greg then goes over the scientific data behind his prejudices, he talks about the reaction his book received from his mother and therapist, he takes your Overheards and Half-A-Mans, and the audience is formally introduced to new producer Jordy.